Schenkkan acted in several film, television, and stage productions from the early 1970s until 1994, after which he began to focus exclusively on writing. In 1992, he received the Pulitzer Prize for Drama for his series of one-act plays entitled The Kentucky Cycle. He later received a Tony Award nomination for the same work.

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Robert Frederic Schenkkan was born in Chapel Hill, North Carolina, and raised in Austin, Texas. He received a Bachelor of Arts degree in Drama, magna cum laude, from the University of Texas at Austin and an Master of Fine Arts in Theatre Arts from Cornell University in Ithaca, New York.

Schenkkan made his stage acting debut playing Captain Tim in a Chicago, Illinois production of Tobacco Road, which ran for 35 performances in 1975. In 1979, he made his off-Broadway debut, playing Wayne Blossom, Jr., in Last Days at the Dixie Girl Cafe. That same year, he was an understudy in the Broadway production of G. R. Point.

In 1984, Schenkkan played John Bates in an off-Broadway production of William Shakespeare's Henry V with Elizabeth Dennehy. From November 1984 through 1985, Schenkkan portrayed Reverend David Marshall Lee in the original, off-Broadway production of Larry Shue's comedy The Foreigner. Christopher Curry also starred in this production.

Schenkkan's other New York stage acting credits included The Taming of the Shrew (1977), The Passion of Dracula (1978), and The Midnight Visitor (1981). His regional theater credits include A Full Length Portrait of America and SWOP at the Actors Theatre of Louisville in Kentucky in 1981, with the latter production co-starring Ken Jenkins (who also wrote the play) and Cristine Rose.[1]

Schenkkan made his first television appearance in 1979, playing Father Wembley in the NBC movie Sanctuary of Fear. His co-stars in this movie included fellow Star Trek: The Next Generation guest actors George Hearn and Saul Rubinek. His next TV appearance was another NBC movie, The Neighborhood, in 1982. This movie also featured William Sadler.

Schenkkan made his feature film debut in the independent 1985 drama Chain Letters with Daniel Davis. This was followed by small roles in the 1986 films Sweet Liberty (with Timothy Carhart and the aforementioned Saul Rubinek) and The Manhattan Project (also with Timothy Carhart as well as JD Cullum).

Schenkkan is the author of ten full-length plays and numerous one-act plays. His most famous work is The Kentucky Circle, a two-part collection of nine one-act plays which explores American mythology for which he received the 1992 Pulitzer Prize for Drama. The Kentucky Cycle was first performed in 1991 at the Intiman Theatre in Seattle, Washington, and transferred to Broadway in 1993. The Broadway production earned Schenkkan nominations from the Tony Awards and the Drama Desk Awards in 1994. The cast of The Kentucky Cycle included Star Trek alumni Gregory Itzin, Scott MacDonald, and Randy Oglesby.

Schenkkan's other plays include: Heaven on Earth, which premiered off-Broadway in 1989 and which won the Julie Harris/Beverly Hills Theatre Guild Award; By the Waters of Babylon, a production of which featured Shannon Cochran; and Lewis and Clark Reach the Euphrates, which premiered in 2006 with Tony Amendola and Jeffrey Nordling in the cast.

In addition to his plays, Schenkkan has ventured into screenwriting. He co-wrote the screenplay for the acclaimed 2002 film The Quiet American, the cast of which featured Tzi Ma and Holmes Osborne. He then wrote the 2004 TV version of Spartacus, which featured Ben Cross. Most recently, he wrote the 2008 mini-series The Andromeda Strain, which starred Daniel Dae Kim.

Schenkkan also is a playwright who authored the stage production "All the Way" about the life and presidency of Lyndon Johnson. The play costarred Michael McKean as FBI director J. Edgar Hoover, Christopher Liam Moore as Walter Jenkins and Ethan Phillips as Speaker of the House John William McCormick of Massachusetts. The play was adapted into an HBO telefilm of the same name featuring Spencer Garrett as Walter Reuther, Hal Landon, Jr assuming Phillips's role as Speaker McCormick, Aisha Hinds portrayed civil rights activist Fannie Lou Hamer, Randy Oglesby was cast as South Carolina senator Strom Thurmond, Stephen Root took over from McKean as Director Hoover, Ray Wise performed as Illinois senator Everett Dirksen and Frank Langella was given the role of Johnson rival and Georgia senator Richard Russell.